


When Jenny met Oz

by emmadilla



Series: The Ballad of Oswald and Jenny [1]
Category: Batman - All Media Types, Batman: The Telltale Series (Video Game), DCU
Genre: AO3 FB Challenge, Anal Sex, Blow Jobs, F/M, Kinktober, Kinktober 2018, Oral Sex, Penis In Vagina Sex, Porn, Prostitution, Sex Work, Shameless Smut, Telltale Universe, Vaginal Sex
Language: English
Status: Completed
Published: 2018-10-08
Updated: 2018-10-08
Packaged: 2019-07-28 02:03:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,845
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16231940
Author URL: https://archiveofourown.org/users/emmadilla/pseuds/emmadilla
Summary: Just when Jenny thinks she's about to spend a cold night alone, Oswald sweeps her off her feet for a whirlwind of a weekend to celebrate his return to the States. Set in the Telltale Universe, just before the first season.





	When Jenny met Oz

**Author's Note:**

> Kinktober day 8 prompt: sex work/prostitution
> 
> I've been developing this character and this story for a while now, and Kinktober has given me some motivation to write about them! This will be the first in a series of stories with Jenny and Oz, though I'm not sure when I'll get to come back to them. But rest assured, their story doesn't end here.

I shivered slightly as I pulled my faux fur coat tighter around me. Winter was coming in Bludhaven, and as if the chill in the air wasn’t enough, a swift wind followed in its wake, lifting my strawberry blond curls and cutting straight through me. My heels clacked on the sidewalk as I walked toward my usual haunts, the echoes of the impact sounding off the brick buildings around me. It had been a while since I’d had to walk the streets for work, but my usual clients were getting caught up in work with the holidays around the corner, and so in my own self-interests and preservation I took to the street once more.

 

A couple of hours later, I hadn’t had too many bites yet. One John had rolled up, but he was way too nervous with the way his eyes were darting everywhere and his hands were restless, and he’d ended up pulling off without taking me up on my offer. No matter. Sometimes you just had to be patient, though I wasn’t sure how patient I could let myself be with how the wind was whipping up. My thin, short purple dress and coat were simply no match. I needed the money, but my will was slowly being broken down with every gust. I had shoved my hands in my coat pockets long ago, and I could no longer feel parts of my face. My legs? Forget about it. Left bare to the elements they felt like frozen blocks, my feet long numb. I had gone for a pair of closed toe heels but really it wouldn’t have mattered, the tiny bit more of protection they offered was negligible. Just when I was about ready to just pack it in and call it a night, a limo turned down the street, and my heart fluttered as I held my breath in anticipation. Not that it wasn’t completely out of the ordinary for high class clientele to be roaming the street, but it was unusual enough where I worked. I put on a soft smile as the limo pulled up to where I was standing, and I went to meet the prospective John, leaning against the window that had been rolled down. “Can I help you?” I purred.

 

The man inside was younger, and actually handsome, and when he spoke he had an obvious accent originating from somewhere in the UK. “You look a little cold out here, love. What’s your name?”

 

“Angel.”

 

Chuckling, he asked again. “I’m sure you are.But what’s your _real_ name?”

 

I visibly hesitated, my smile faltering for just a moment. I didn’t just give out my real name to my clients. To my recollection, perhaps only one or two knew, and they were some of my oldest ones, from back before I hardly knew what I was doing. Everyone just knew me as Angel now. They didn’t question it, didn’t wonder about it, or if they did they kept it to themselves. They contracted me, I did my job, and then we went our separate ways, no questions asked. I didn’t ask them who they were or what they did, and if I ended up finding out it was because they spontaneously told me. I didn’t really care that much, to be honest, but hey I wasn’t one to tell a guy how to spend his money. If he wanted to take up half his time just talking, then that was on him. But in all my time working, no one had ever asked about _me_. And so I was taken aback by this strange young man.

 

Sensing my hesitation, he pulled out a couple of bills and held them out to me. “How about $200 for a name?”

 

Two hundred dollars, just for my name? Shit, I wasn’t about to protest. I was in no position to say no to money coming my way. Taking the two bills and throwing caution to the wind, I replied, “Jenny.”

 

“Jenny,” he repeated. “How would you feel about spending the weekend with me? Tonight, tomorrow, and Sunday. I’ll cover all expenses and drop you off wherever you want Monday morning.”

 

I raised my eyebrows at the prospect. No one had ever contracted me for _days_ at a time before, the most being one night at a time. But if he was willing to pay, then I wasn’t about to say no. “It’s $300 per night, handsome.”

 

He took out some more bills and offered them. “How about $1,000 even? I’m celebrating this weekend, want to have a lot of fun.”

 

This was the strangest negotiation I’d ever done, but with the money being offered, how could I protest? Twelve hundred off the top, plus all expenses paid? It almost sounded too good to be true, but he was offering it up front. There was a small voice of warning trying to protest, but I silenced it by reaching out and taking the money. “Well let me help you celebrate, doll.”

 

“Good girl. Now come on and get in, you look cold, love.”

 

I swore I had never felt so grateful for heating in all my life, except for perhaps when I had just been starting out and had to walk the streets every night. That first blast almost hurt, but fuck it hurt so _good_ as I climbed into the limo. The John directed the driver to go back to _the hotel_ , and I recognized it as one of the swankiest places in all of Bludhaven. He was definitely a high roller, and in my mind I was busy calculating how much I would be willing to do for what he gave me. I didn’t have too many hard no’s as it was, it was all just a matter of how much someone was willing to pay for it. But for everything he was offering, just about anything was on the table as far as I could figure. If he happened to approach one of my limits then I figured we could discuss it then. But until then, he obviously wanted a companion for the time being, and so I would be that companion for him.

 

He took one of my hands in his as I settled in, and I couldn’t say that his warm fingers were unwelcome, though I was surprised. It seemed he was touchy feely, which was fine. If that’s what he wanted, then that’s what he would get. His brow furrowed as his fingers slid over mine. “I wasn’t wrong, then. You poor thing, you’re about frozen. Couldn’t take the night off, eh?”

 

I smirked. “Girl’s gotta make a living.”

 

“Of course. Well don’t worry, we’ll be in a nice, warm penthouse soon.”

 

He wasn’t lying, either. Maybe ten minutes later and we were walking through the doors to The Ritz. I’d never set foot in the luxury hotel before and felt a bit out of my element, but my companion was easy to take charge and ushered me into a private elevator before sliding his card to take us up to the top floor. I stood close to him in the elevator and he seemed to like that, flashing me a grin. The room itself … well, luxurious only began to describe it. Whoever had designed it had gone into excruciating detail, making sure that nothing was overlooked. Everything had a place and that place was polished and smooth or covered in rich materials. I set my purse gently on the table as my client sauntered over to the wet bar, scrounging a couple of glasses and popping the cork on a bottle of champagne. As he made his way back over to me, I was a bit surprised. I had been expecting to more or less get down to business once we arrived, and was honestly a bit surprised that he hadn’t wanted to start things in the car. But hey, he was the one paying, I supposed, and I took the the flute he offered. “What are we drinking to?”

 

He raised his flute ever so slightly. “To success, love.”

 

“Success.” Our glasses clinked and we shared the toast, after which I then expected him to make a move or request to do something, but instead he simply wandered over to the couch, patting the space next to him.

 

Shucking my jacket as the cold started to leave me, I followed his lead and joined him, crossing my leg so that I leaned toward him. He slid an arm around me as we drank and he asked, “Warming up now?” I nodded and he grinned. “I wager this is a damn sight better than that street corner.”

 

“By leaps and bounds.”

 

He let out a soft, barking laugh. After taking another sip, he asked, “Don’t you want to know my name?”

 

I smiled softly, my fingers tracing the stem of my glass. “Only if you want to.”

 

His eyebrow quirked in surprise. “You have Johns that don’t tell you their name?”

 

I shrugged. “Some prefer to be as discreet as possible. It’s no problem. Client confidentiality is important to me.”

 

Chuckling, he introduced himself anyway. “It’s Oswald. Oswald Cobblepot. But you can just call me Oz.”

 

“Oz?” I chuckled. “You gonna tell me you’re some kind of wizard next?”

 

He snorted. “Care to guess how many times I’ve heard that?”

 

“Probably as many times as I’ve been asked if I’m really from the block.” I had long since cursed Jennifer Lopez for that goddamn song, especially as it had come out when I was a scrawny little teenager who really didn’t need any more reasons to be teased.

 

He grinned as he lifted his glass once more. “Point taken.” We sipped our drinks in silence for a moment before he asked. “You hungry? I’m about starved, myself. Just got in and all.” I hadn’t eaten for a while before I’d left, not wanting to have to leave my post in search of a bathroom, and as if in response to the question my stomach growled. He laughed as he commented, “I suppose that’s my answer. You vegetarian or anything?” I shook my head and he replied, “Good. I’ve heard the prime rib here is excellent. I’ll go put in an order, then.” Winking he stood and walked over to the room phone, picking up and dialling down to the kitchen. I continued to sip on the champagne quietly, not really sure what to do with myself. I wondered if he was waiting for me to make a move? Normally, the guys I was with knew what I was there for and went after me as soon as we were somewhere private, even if somewhere private was in the backseat of a car in a dark alley. I’d notice him look me up and down once or twice, but other than that and his close proximity, our encounter thus far seemed entirely platonic. It was strange, but I supposed if this was what he wanted then this is what he would get. The whole concept was still so foreign to me, and if I was honest I felt a little off balance by this whole thing.

 

I wasn’t sure who had told him about the prime rib, but whoever it was they were certainly right. The meat practically felt apart and melted in my mouth. Oz seemed to enjoy just as much as me, and by the time we finished I wondered if I’d ever be hungry again. This whole thing was already worth it, as far as I was concerned, and I wondered if he’d been saving more lascivious activities for after dinner, but when he simply poured us another drink and settled back into the couch, I was starting to question everything with him. Why was he doing all of this? Why go to all these lengths just for a sex worker? Was he truly that hard up for friends that he had to buy his companionship? He was young and handsome and charming, I had a hard time believing he couldn’t have just gone to a bar and picked up someone for free. And yet he’d dropped twelve hundred just like that to buy the company of a stranger. Oz certainly seemed a mystery that I pondered as we sat there and drank.

 

As I finally drained my glass, he took it from me and, seemingly picking up on my internal meditation, asked, “Everything alright, love?”

 

I nodded, flashing him a smile. “Of course.”

 

While most would have simply taken me at my word and written it off, he didn’t quite seem to buy it. “You sure? You’ve been quiet since dinner.” His thumb stroked my bare shoulder as he added, “I want you to be comfortable.”

 

It was my turn to raise an eyebrow. “Really?”

 

“Why wouldn’t I?”

 

I had to laugh at that. “In my line of work, we only serve one purpose. Some like to small talk here and there, some even spill their whole lives, but ultimately it all comes down to one thing.”

 

He shrugged. “That mean I can’t woo you?”

 

That surprised me, turning me completely off balance. “Sorry, I … I’m not really used to being _wooed_.”

 

He smiled at me, gently this time, genuine. “Just because I’m paying for you doesn’t mean you don’t deserve to be treated well. I take it you don’t get that much.”

 

I chuckled, shaking my head. Oz was certainly something else. “I can’t afford to be too picky with clients, Oz. I do what they want, as long as they can pay for it.”

 

“Well, for tonight, let’s forget all that, shall we? We’re just two people, you and I, and that’s all we need to be.”

 

Fuck it. Carpe diem and all that shit. He was certainly paying me enough to not care about how he was going about this weekend, and so I wouldn’t. Most of my clients didn’t care that I was a sex worker, and hell some even got off on it. He was the first who wanted to actually act like he wasn’t a John and I wasn’t a person whose company he’d bought. But hey, more power to him. And if I was lucky and he enjoyed this whole thing, then maybe I’d get repeat business. I wasn’t averse to that at all.

 

Tugging me close to him, he murmured, “C’mere, love.” He reached up with his other hand and cupped my cheek, leaning in for a kiss. It wasn’t something a lot of clients wanted to do, seen asa little too personal, a little too intimate, but it seemed that was not so for Oz. Instead of sloppy and hesitant like the few kisses I did get, he was sure and smooth, working my lips over gently until he naturally got them to part, at which point he dove in. It was nice, to be claimed like that, and the motion actually made me glad we were sitting because I would have found it to be a hard thing to stand after this. My hand wandered over the front of his shirt, gently popping buttons as we built up to what was coming next. It was inevitable, after all. Now that we were on a little bit more familiar territory, I felt more sure in my actions, and moved to straddle him. He didn’t stop me, and it gave me better access to his shirt and, of course, his belt. He made no move to stop me as I unzipped his pants and worked my hand inside, finding his hardening length and giving it a few strokes. By the feel of him, while he wasn’t my biggest client, he wasn’t small. It made no real difference as I kept a variety of condom sizes on me in my purse to cover a range of men that might solicit me. The “oh, sorry, must have left the condom in my other pants” excuse wasn’t going to fly with me. I had safe sex or no sex and if a guy wanted to protest too much, I was more than willing to leave the money and walk out the door. It seemed I didn’t have to worry about it, however, as Oz slipped a familiar foil packet out of his pants pocket and held it up between us. “Care to put that on?”

 

“My pleasure,” I purred, taking the packet and examining it briefly for any pinpricks before I tore it open. He furrowed his eyebrows in confusion and I explained, “An asshole once tried to get me to use a condom he’d poked a hole through. I inspect them every time now. Nothing against you.”

 

Chuckling, he commented, “Sounds like you need an upgraded clientele.”

 

“Ain’t no other gig pays as good, honey. If there was, I’d be workin’ it.” It was true. I’d graduated high school and had attempted to go to college while working as a cocktail waitress, but between all the stress of class assignments and trying to get enough hours to pay bills, I felt like I was going crazy. When I saw that other girls had no problems with cash flow and realized why, I dropped out of college. I hadn’t even decided on a major, had no clue what I wanted to do with my life. I just wanted to be comfortable and happy, and I was, so I figured fuck it. No outrageous student loans to pay back, no laborious ladder climbing or ass kissing … unless, of course, they wanted to pay extra for that.

 

I sidled off of his lap and knelt between his legs as I pulled out the condom. Time for my party trick, the one that kept them coming back. I settled it just on the tip before I leaned over and pushed it down his entire length with my lips and mouth. I wasn’t entirely without a gag reflex, but it was minimal, and I’d been able to work on it over the years. He seemed quite pleased at it as he let out a loud moan, his hips twitching upward ever so slightly as I hit the base. It was time to go to work, and considering the money he’d dropped, I pulled out all the stops, not wanting him to regret paying me so much. I worshipped his cock like it was the only one I’d ever had, and the way his eyes slitted as he watched me sent a thrill of pride shoot through me. His hands played with my loose curls as I worked, his head sometimes dropping back to rest on the back of the couch. He eventually pulled me off of him and said, “Enough. I don’t want to finish yet.”

 

I stood and grasped the hem of my dress, pulling the sheath off in one go. Thank fuck for body clinging fabric that was also stretchy as fuck, they were a lot easier to get out of quickly. Reaching behind me, I unhooked the satin bra and let it fall off, Oz’s eyes following my every movement. I pushed down my underwear just enough to where they could fall down on their own before stepping out of them and moving to straddle him. He helped line himself up before I lowered myself on him and he settled his hands on my hips as I started to ride him. He met my hips with his, and I was pleasantly surprised he was this reciprocative. Some men just wanted to lie there and let me work on them, which was fine. They were paying for it and as long as they walked away happy, that was all I cared about. And Oz was going to get his money’s worth out of this weekend.

 

His hands eventually made their way up my body to cup my breasts before he leaned in and started licking and sucking on them. Fuck, this was getting to be one of my best sessions already and this was only the first night. I sometimes had to fake my arousal for some clients who didn’t want to put in any effort of their own, but that was not needed here. Every moan and whine he drew from me was genuine. Biting his lip, he reached up and pulled me down to him, locking lips with me as he tightened an arm around my waist and flipped us onto a lying position on the couch.

 

Sitting up, he hooked my left leg up onto his shoulder, bestowing my foot a kiss just on the outside of my sparkly gold heels. Throwing off his shirt, he leaned down once again as he pumped in and out of me, steadily increasing his pace. His cock was curved ever so slightly, just enough that it hit that spot just right inside of me and started building that wave. One of his hands reached between us and started rubbing at my clit, and I jerked in surprise at his consideration. His eyes locked onto mine as we rutted against each other in earnest, descended into that age old dance. It was steady push and pull rhythm, and I found my own orgasm bubbling up inside me as he moaned above me, a random bead of sweat falling off of his forehead and onto my chest. “Oz,” was the only warning I could give him as my back arched off the couch, my orgasm taking me and wrenching my body with a surprising intensity. His hips stuttered as I clenched around him, and he only kept pumping for a few more minutes until he found his own release.

 

As I was still coming down from my own high, I realized that this might just be the most unique John I’d ever taken on. And I didn’t quite think that a bad thing.

 

After a mutually taken shower - during which there was some serious heavy petting - and after both of us used the facilities, it was quite late, indeed. I wouldn’t have protested going to bed, but with the way Oz’s eyes traced over my still naked body, I knew he had at least one more round in him yet. Smiling, I sauntered over to the bed that he was lying on and leaned down to give him a kiss before I asked, “Once more before we call it a night?”

 

With the way he grinned, I had my answer. “Do you … do you do anal?”

 

Nodding, I replied, “Let me go get the lube in my purse.”

 

Anal was one of those things that was usually guaranteed to net you more money as opposed to just a blowjob or penis in vagina sex. As a result, I always kept a small bottle or two of lube in my purse, along with my bevy of condoms, just in case a John wanted to indulge. Normally I would charge extra than what I was already charging, but since Oz had overpaid me several times over - and treated me very well, besides - the thought didn’t even cross my mind.

 

Crossing back over to the bed, Oz was already hard and ready to go, so I slipped on the condom and asked, my voice low and sultry, “How do you want me?”

 

His teeth nipped at my earlobe before he responded, “Hands and knees, love.”

 

I assumed the familiar position, laying my head against the mattress as I jutted the rest of my lower body upwards. I could practically feel the heat coming off of him as he got himself into position before he opened the bottle of lube and started applying it where it was needed. He briefly penetrated me with two fingers before he pulled out and positioned the tip of his cock near my second entrance. I was so used to this kind of sex, I didn’t really need prep, and so I ordered my body to relax as he slowly started to penetrate me.

 

He moaned as he buried himself in me, commenting under his breath, “Fuck, you’re awfully tight.” I grinned and bit my lip, closing my eyes as he slowly pulled almost all the way out before pushing himself back in. It took a little while of slow strokes - along with some reapplication of lube - before he felt comfortable enough to set a more regular pace. He settled his hands on my hips, occasionally massaging and cupping my ass as he fucked me. Fuck but I had to admit he filled me up just perfectly, not too big, not too small, and I was into it just as much as he was.

 

After some time, he reached down and tugged on my upper body, murmuring, “C’mere, love.” He pulled me up to an upright position, holding my body against him as he fucked me. He was able to easily kiss me from this position and even reached down to play with my clit as he started fucking me hard and fast. The room practically echoed with the sounds of our combined moans and our skin was hot and slick pressed up against the other. Oz had a downright predatory look in his eye as he kissed and nipped at my neck, paying attention to what made me shudder and react favourably. It was a welcome and unexpected change from the usual Johns that I took on, that he was so concerned about if I was enjoying this as much as he was. I mean, of course, it was usually all about the John and what he wanted and how he felt. But it was nice to have someone be so obviously considerate of my own enjoyment. For so long, fucking had just been a job for me, just something that I did to bring in the money. But somehow … somehow with Oz, it just felt different. I couldn’t even put my finger on it, on why it was different, but it was.

 

I started trembling as I valiantly fought off my orgasm, not wanting to give in just yet, because it felt too good. I focused instead on Oz’s lips, which he had brought back to mine, kissing me long and deep. I couldn’t stave it of forever, though, and he picked up on it. Parting our lips, he murmured, “Ya close? Gonna come on my cock? Go ahead, be a good girl, come for me.” It didn’t take much prodding as he nuzzled my neck, and I laid my head on his shoulder as my orgasm rocked through me, digging my fingernails into his arm with the intensity. He didn’t seem to mind, or even notice, as he buried his face in my neck, whispering, “Yes, yes, that’s it …” Squeezing me tightly, he measured out perhaps a dozen more strokes before he snapped his hips and buried himself as deeply as he could inside me as he came.

 

It took us even longer to come down than the first round, but we settled in for the night against each other, his arm wrapped around me as he held me close. It was strange, but nice, and I decided to just enjoy the hell out of it while I could.

 

The rest of the weekend passed in a blur. Sometimes he would take me out somewhere and we’d hang out, other times we’d just hole up in the room and fuck, but by Monday morning, I’d say he’d gotten his money’s worth. I was almost disappointed that the weekend was over, truth be told, it had been so much fun and so nice to actually relax around someone. I still couldn’t explain how or why I felt so comfortable around Oz, but I secretly hoped he might become a regular. Not because I wanted him to throw more money at me, though it was nice, but because there was just something about him, something genuine and real and passionate that appealed to me.

 

As I packed up the few things I’d left out of my purse that Monday morning, out of the blue, Oz said, “Come with me to Gotham. I’ll pay you well, make it worth your while.”

 

If he had asked me to go anywhere else with him, I would have immediately said yes. But Gotham conjured up long past images that I’d tried so hard to let go of, and I shook my head as I zipped up my bag. “Sorry, Oz. No amount of money could make me want to go back there.”

 

I worried that I had upset him, and he didn’t exactly look happy about it, his eyebrows furrowed in disappointment. But it soon passed and he flashed me a grin. “Can’t blame a guy for tryin’.”

 

Smiling, I walked over to where he was lounging on the couch, leaning over to kiss his cheek before I whispered, “But if you ever find yourself back in Bludhaven, feel free to look me up.”

 

By the sly grin on his face, I knew that we would meet again.


End file.
